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Diisopropylethylamine → (+/-)-Tert-butyl 1-[3-({cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}-amino)benzyl]cyclopropanecarboxylate

HRID 1475659
ノート
印刷プレビュー

反応式

HRID 1475659 の反応式
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:40][C:41]1[CH:42]=[C:43]([CH:55]=[CH:56][CH:57]=1)[CH2:44][C:45]1([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:47][CH2:46]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)[C:7]([NH:40][C:41]2[CH:42]=[C:43]([CH:55]=[CH:56][CH:57]=2)[CH2:44][C:45]2([C:48]([O:50][C:51]([CH3:54])([CH3:52])[CH3:53])=[O:49])[CH2:47][CH2:46]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58136514tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylateHCID 67078122(+/-)-Cyclopentyl[4-(trifluoromethyl)phenyl]acetic acid

生成物 1

HCID 68170307
(+/-)-Tert-butyl 1-[3-({cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}-amino)benzyl]cyclopropanecarboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

3.0 g (11.02 mmol) of (+/−)-cyclopentyl[4-(trifluoromethyl)phenyl]acetic acid were dissolved in 16.0 ml of DMF, and 1.79 g (13.22 mmol) of 1-hydroxy-1H-benzotriazole hydrate were added. The mixture was cooled to 0° C., and 3.8 ml (22.04 mmol) of N,N-diisopropylethylamine and 3.41 g (13.77 mmol) of tert-butyl 1-(3-aminobenzyl)cyclopropanecarboxylate, dissolved in a little DMF, were added. 5.03 g (13.22 mmol) of HATU were then added in several portions, and the reaction mixture was slowly warmed to RT and then stirred at RT for 3 h. The reaction was then added to water. After phase separation, the aqueous phase was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→10:1). This gave 4.89 g of the target compound (88.5% of theory).

後処理

  1. additionwere added
  2. temperaturethe reaction mixture was slowly warmed to RT
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted three times with ethyl acetate
  5. washthe combined organic phases were washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→10:1)

出典と根拠

ORDレコード
ord-467231b685384fdea490742b933dfb17
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018258B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート